Carbopyronone Compounds Useful as Diagnostic Adjuvants
AssigneeLife Technologies Corporation
InventorsKyle Gee, Hee Chol Kang, Wenjun Zhou, Bradley Dubbels, Michael Olszowy, Michael O'Grady
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Abstract
Described herein are fluorescent compounds and methods and comprising these compounds. The compounds disclosed herein are carbopyronine reagents that fluoresce in the red portion of the UV/VIS spectrum and provide bright fluorescence intensity, uniform cell staining, and good retention within live cells as well as low toxicity toward cells.
Claims28
A compound of structural formula (I):
- or a pharmaceutically acceptable salt thereof, wherein
- R12 and R13 are each independently H, alkyl, substituted alkyl, -L-Rx, or -L-Sc;
- R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R14, R15, and R16 are each independently H, halogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, acylamino, acyloxy, amino, substituted amino, aminocarbonyl, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyl, aminosulfonyloxy, aminosulfonylamino, amidino, carboxyl, carboxyl ester, (carboxyl ester) amino, (carboxyl ester) oxy, cyano, alkylcarboxylate, hydroxyl, nitro, sulfo, sulfoalkyl, substituted sulfoalkyl, sulfonyl, substituted sulfonyl, sulfonyloxy, thioacyl, thiol, alkylthiol, substituted alkylthiol, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, substituted heterocyclyl, -L-Rx, or -L-Sc;
- or
- R7 taken together with R14 are part of an optionally substituted 5- or 6-membered ring;
- R8 taken together with R15 are part of an optionally substituted 5- or 6-membered ring;
- R9 taken together with R11 are part of an optionally substituted 5- or 6-membered ring;
- R10 taken together with R16 are part of an optionally substituted 5- or 6-membered ring;
- L is a linker;
- Rx is a reactive group;
- and
- Sc is a conjugated substance.
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A method for tracking cell proliferation, differentiation, and/or function, the method comprising the steps of:
- a) incubating a mixture of cells and a compound of structural formula (I):
- or a pharmaceutically acceptable salt thereof, wherein
- R12 and R13 are each independently H, alkyl, substituted alkyl, -L-Rx, or -L-Sc;
- R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R14, R15, and R16 are each independently H, halogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, acylamino, acyloxy, amino, substituted amino, aminocarbonyl, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, aminocarbonyloxy, aminosulfonyl, aminosulfonyloxy, aminosulfonylamino, amidino, carboxyl, carboxyl ester, (carboxyl ester) amino, (carboxyl ester) oxy, cyano, alkylcarboxylate, hydroxyl, nitro, sulfo, sulfoalkyl, substituted sulfoalkyl, sulfonyl, substituted sulfonyl, sulfonyloxy, thioacyl, thiol, alkylthiol, substituted alkylthiol, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, substituted heterocyclyl, -L-Rx, or -L-Sc;
- or
- R7 taken together with R14 are part of an optionally substituted 5- or 6-membered ring;
- R8 taken together with R15 are part of an optionally substituted 5- or 6-membered ring;
- R9 taken together with R11 are part of an optionally substituted 5- or 6-membered ring;
- R10 taken together with R16 are part of an optionally substituted 5- or 6-membered ring;
- L is a linker;
- Rx is a reactive group;
- and
- Sc is a conjugated substance;
- b) providing a stimulus to the mixture to elicit a fluorescent signal;
- and
- c) analyzing the stimulated mixture.
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Dependencies are inferred from the claim text.